Improved racemate resolution of pentan-2-ol and trans-(Z)-cyclooct-5-ene-1,2-diol by lipase catalysis

Abstract : Lipases are important catalysts in chiral synthesis due to their wide substrate recognition combined witha high stereoselectivity. We demonstrate here that the state, free or immobilized, of Candida antarcticalipase B (CaLB) affects enantioselectivity and also alters the temperature dependancy of the enzyme. Thisindicates that CaLB undergoes various conformations induced by its interaction with the different immo-bilization supports studied. Molecular imprinting experiments, using immobilized enzyme co-dried withmimic substrate molecules, enhanced the enantiomeric ratio two-fold or three-fold, depending on theimmobilization support. The structure of the acyl donor has a pronounced effect on CaLB catalyzed res-olution, due to the proximity of the acyl and alcohol moieties during catalysis. When the acylation ofpentan-2-ol was examined, we found that the 3C methyl propanoate donor afforded the highest resolu-tion. Trans-(Z)-cyclooct-5-en-1,2-diol was used as a model racemic substrate to study the ability of lipaseto catalyze the resolution of difunctionalized compounds. There was a clear enhancement in the enan-tiomer selectivity of the biotransformation of the diol when vinyl butanoate is used as the acyl donor. Theconversion and enantiomeric excess of (1R,2R)-monoacetates were enhanced, using immobilized CaLB,when the chain length of the donors increased from C2 to C4.
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Submitted on : Wednesday, January 11, 2017 - 5:44:50 PM
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Marianne Graber, Hervé Rouillard, Régis Delatouche, Najla Fniter, Belsem Belkhiria, et al.. Improved racemate resolution of pentan-2-ol and trans-(Z)-cyclooct-5-ene-1,2-diol by lipase catalysis. Journal of Biotechnology, Elsevier, 2016, 238, pp.60-68. ⟨10.1016/j.jbiotec.2016.09.010⟩. ⟨hal-01432549⟩

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